A letter from my future self

I’ve been meaning to write a new letter for years now, but something inside me resisted it. Perhaps I’ve been afraid of what’s ahead, or afraid that writing down what success will look like is presumptuous, something not yet earned. 

Recently, however, someone posted that this letter exercise in Week 7 was hard for them, and that gave me the nudge I needed. I thought, If I can’t do it, how can I ask others to try? So here it is. To help me write my letter, I put the timeframe further out than usual. That made it safer for me somehow.

The instructions say to write this letter for yourself, not to impress someone else. That’s what I tried to do. I share it here to offer another public example of what such a letter might look like, and also to serve as a visible reminder of what I aspire to accomplish.

April 24, 2034

Dear John,

Well, here we are: 2034. It’s a number I thought I’d only see in Science Fiction stories. (I still remember when Orwell’s 1984 was a distant future.) Now I’m 70 years old. More precisely, we are 70. Congratulations to both of us for making it this far.

A lot has happened, some of which you hoped for, and some which you didn’t dare to dream about at the time. Brace yourself, though. It wasn’t easy.

Our family is doing well. The kids are great. As you grew to be more comfortable in your own skin, that made it easier for others to be comfortable with and around you. It took much longer than we both might have hoped, but you made steady progress. The yoga and meditation helped. The move to Japan helped a lot, too. Life is simpler here. You became clearer about what’s important and why.

I remember how fragile you were when you started on your own. You were so worried all the time, about making a living, about being a good provider, about your status after having lost your job. If it wasn’t for your wife’s strength, support, and love, you never would have made it through this period. Be good to her.

The funny part is that things picked up when you stopped trying so hard to make it all work. When you focused on the contribution instead - on making things other people found genuinely helpful and useful - all of the other things you wanted flowed from that. 

To be sure, there were blow-ups. Some were near fatal to your business and movement. But then someone would send you a note, saying that you made a difference, and that was enough for you to keep going. The kindness of your WOL community was a source of strength. Never underestimate how important they are. 

A key turning point was around 2019 or 2020. Back then, you were like a little boy on a diving board, looking down, uncertain whether to make the leap or climb back down to earth. Some big companies were Working Out Loud, but you were cautious, always unsure or afraid of whether the little success you had would last. 

Then you leapt. You started to work with people in factories, hospitals, and schools, looking to help people who need it most. You expanded WOL to include practicing self-compassion, and enabling people to make the work they do more purposeful.

In the last fifteen years, you reached a million people. That’s a big number In ways large and small, you changed how they related to themselves, to others, and to they work they do. You can let yourself be proud of that.

If I have any advice for you, it’s this: Think ten times bigger. A hundred times bigger. Worry less about making mistakes, or about “who am I to attempt such a thing?” Dare to make a difference. Not for yourself or for your business, but for other people. The world could still use it, maybe now more than ever.

With love and respect.

Your Future Self

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The first draft of the rest of your life

The subject of the email was “Need your help.” Since it was sent by a strong, confident friend who had never asked for help before, I was worried. It turned out it wasn’t a crisis, but she was stuck on something. “I’m in big trouble…do you have time?” So we scheduled a call.

The problem? She had committed to submitting a paper for publication, and she couldn’t get started. Though she has a lot to say on the subject, she had struggled for weeks to make any progress and now the deadline was looming. Her anxiety was evident.

I thought of the many bits of advice I had benefitted from and might share, and then I discarded all of it.

“Open up your laptop,” I said. “Let’s start right now.”

At first we just talked about the topic, and after a few minutes a theme emerged. We exchanged ideas for a phrase or sentence that might capture it until we came up with a headline that felt good to her. “Great,” I said. “Write that down.”

We moved on to headings. What were the main points she was trying to make? She talked about a wide range of ideas, including some resources she found helpful. It was scattered at first. She was still overwhelmed. I listened, and reflected back whatever major points I heard. When one made sense to her, she wrote it down. Then we came up with another. “That reminds me!” she said, erupting with ideas now. She began recalling related things she had written and read and thought about before.

Soon there was less talking and more typing. Her energy had shifted from nervous to excited, and she was still writing as we hung up. A few weeks after our call, she sent me a note that she had finished it. It wasn’t perfect, she told me, and she would do it differently next time, but she was glad for the chance to learn and get better.

Since our call, I’ve been thinking of how my friend’s experience is a metaphor for how many of us live our lives. We struggle to think through what we want our life to be like. We may have ideas but it can be hard to put them into a coherent picture. And we may feel time is running out.

Waiting doesn't help. The only way out is through. Maybe you start with writing a letter from your future self, or describe your perfect month, or do whatever exercise would help you capture the first draft of an intentional life. It may not be exactly right, but that step attunes your attention and opens you up to next steps and new possibilities.

As the poet Mary Oliver asked

Tell me, what is it you plan to do with your one wild and precious life?

Voice your intention. Pick up your journal or laptop and begin writing. Clip pictures from magazines and craft a vision board. Call a friend if you need to. Let’s start right now.

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